Antenna biphenols: Development of extended wavelength chiroptical reporters

Journal of Organic Chemistry

Volumn 81, Issue 3, 2016, Pages 1185-1191

  Bentley, Keith W ^a   Joyce, Leo A ^b   Sherer, Edward C ^b   Sheng, Huaming ^b   Wolf, Christian ^a   Welch, Christopher J ^b  

^a GEORGETOWN UNIVERSITY   (United States)

^b MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMISTRY; ORGANIC COMPOUNDS;

ABSOLUTE CONFIGURATION; ASYMMETRIC TRANSFORMATIONS; CONVENTIONAL METHODS; ENANTIOPURITY; ENANTIOSELECTIVE; GUEST MOLECULES; INTERFERING SIGNALS; SENSOR READOUT;

ANTENNAS;

EID: 84957828200     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b02716     Document Type: Article

References (33)

1. Subramanian, G. Chiral separation techniques: a practical approach, 2 nd ed.; Wiley-VCH: Weinheim, Germany, 2001.
2. Schurig, V. J. Chromatogr. A. 2001, 906, 275
3. Traverse, J. F.; Snapper, M. L. Drug Discovery Today 2002, 7, 1002 10.1016/S1359-6446(02)02436-4
4. Welch, C. J. In Preparative Enantioselective Chromatography; Cox, G., Ed.; Blackwell: London, 2005; pp 1-18.
5. Matile, S.; Berova, N.; Nakanishi, K.; Novkova, S.; Philipova, L.; Blagoev, B. J. Am. Chem. Soc. 1995, 117, 7021 10.1021/ja00131a033
6. Huang, X.; Fujioka, N.; Pescitelli, G.; Koehn, F. E.; Williamson, R. T.; Nakanishi, K.; Berova, N. J. Am. Chem. Soc. 2002, 124, 10320 10.1021/ja020520p
7. Nieto, S.; Lynch, V.; Anslyn, E. V.; Kim, H.; Chin, J. J. Am. Chem. Soc. 2008, 130, 9232 10.1021/ja803443j
8. Holmes, A. E.; Das, D.; Canary, J. W. J. Am. Chem. Soc. 2007, 129, 1506 10.1021/ja0666147
9. Li, X.; Burrell, C. E.; Staples, R. J.; Borhan, B. J. Am. Chem. Soc. 2012, 134, 9026 10.1021/ja2119767
10. Dragna, J. M.; Pescitelli, G.; Tran, L.; Lynch, V. M.; Anslyn, E. V.; di Bari, L. J. Am. Chem. Soc. 2012, 134, 4398 10.1021/ja211768v
11. Zhang, P.; Wolf, C. Chem. Commun. 2013, 49, 7010 10.1039/c3cc43653e
12. Irfanoglu, B.; Wolf, C. Chirality 2014, 26, 379 10.1002/chir.22332
13. Bentley, K. W.; Nam, Y. G.; Murphy, J. M.; Wolf, C. J. Am. Chem. Soc. 2013, 135, 18052 10.1021/ja410428b
14. Pfeiffer, P.; Quehl, K.; Tappermann, F. Ber. Dtsch. Chem. Ges. B 1930, 63, 1301-1308 10.1002/cber.19300630604
15. Pfeiffer, P.; Quehl, K. Ber. Dtsch. Chem. Ges. B 1932, 65, 560-565 10.1002/cber.19320650410
16. Canary, J. W.; Mortezaei, S.; Liang, J. A. Coord. Chem. Rev. 2010, 254, 2249-2266 10.1016/j.ccr.2010.03.004
17. Joyce, L. A.; Maynor, M. S.; Dragna, J. M.; da Cruz, G. M.; Lynch, V. M.; Canary, J. W.; Anslyn, E. V. J. Am. Chem. Soc. 2011, 133, 13746 10.1021/ja205775g
18. Joyce, L. A.; Canary, J. W.; Anslyn, E. V. Chem.-Eur. J. 2012, 18, 8064 10.1002/chem.201103592
19. Leung, D.; Kang, S. O.; Anslyn, E. V. Chem. Soc. Rev. 2012, 41, 448 10.1039/C1CS15135E
20. Wolf, C.; Bentley, K. W. Chem. Soc. Rev. 2013, 42, 5408 10.1039/c3cs35498a
21. Wezenberg, S. J.; Salassa, G.; Escudero-Adan, E. C.; Benet-Buchholz, J.; Kleij, A. W. Angew. Chem., Int. Ed. 2011, 50, 713-716 10.1002/anie.201004957
22. Anyika, M.; Gholami, H.; Ashtekar, K. D.; Acho, R.; Borhan, B. J. Am. Chem. Soc. 2014, 136, 550-553 10.1021/ja408317b
23. Bentley, K. W.; Nam, Y. G.; Murphy, J. M.; Wolf, C. J. Am. Chem. Soc. 2013, 135, 18052 10.1021/ja410428b
24. Sonogashira, K. J. Organomet. Chem. 2002, 653, 46-49 10.1016/S0022-328X(02)01158-0
25. Heck, R. F.; Nolley, J. P., Jr J. Org. Chem. 1972, 37, 2320 10.1021/jo00979a024
26. Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; et al., Gaussian 09, revision A.1; Gaussian, Inc.: Wallingford, CT, 2009.
27. Bauernschmitt, R.; Ahlrichs, R. Chem. Phys. Lett. 1996, 256, 454 10.1016/0009-2614(96)00440-X
28. Lingenfelter, D. S.; Helgeson, R. C.; Cram, D. J. J. Org. Chem. 1981, 46, 393 10.1021/jo00315a033
29. Bentley, K. W.; de los Santos, Z. A.; Weiss, M. J.; Wolf, C. Chirality 2015, 27, 700 10.1002/chir.22489
30. Moreno, E.; Nolasco, L. A.; Caggiano, L.; Jackson, R. F. W. Org. Biomol. Chem. 2006, 4, 3639 10.1039/b609360d
31. Annamalai, V.; DiMauro, E. F.; Carroll, P. J.; Kozlowski, M. C. J. Org. Chem. 2003, 68, 1973 10.1021/jo025993t
32. Eelkema, R.; Feringa, B. L. J. Am. Chem. Soc. 2005, 127, 13480 10.1021/ja054352n
33. Alexakis, A.; Polet, D.; Rosset, S.; March, S. J. Org. Chem. 2004, 69, 5660 10.1021/jo049359m